Cinobufotenine
Chemical compound
From Wikipedia, the free encyclopedia
Cinobufotenine, also known as bufotenium, bufoteninium, or 5-hydroxy-N,N,N-trimethyltryptaminium, is a quaternary ammonium cation as well as a derivative of 5-hydroxytryptamine, It is the parent compound for bufotenidine. The compound is a powerful stimulant of the parasympathetic ganglia, activates nicotine-sensitive acetylcholine receptors, сinobufotenine is highly active on the ileum.[1] It is contained within the skin of certain toads (Bufo gargarizans).[2][3]
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| Names | |
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| IUPAC name
2-(5-hydroxy-1H-indol-3-yl)ethyl-trimethylazanium | |
| Other names
Bufotenium; Bufoteninium; 5-HTQ; 5-Hydroxy-N,N,N-trimethyltryptaminium | |
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| Properties | |
| C13H19N2O | |
| Molar mass | 219.308 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bufotenidine, also known as 5-hydroxy-N,N,N-trimethyltryptammonium (5-HTQ) or as cinobufagine, is an indole toxin related to bufotenin, serotonin, and other tryptamines which is found in the venom of a variety of toads.[4][5] It acts as a selective serotonin 5-HT3 receptor agonist, and has been used in scientific research to study the function of the serotonin 5-HT3 receptor, though this use has been limited by the fact that, as a quaternary amine, it is unable to readily cross the blood-brain-barrier and hence is peripherally selective.[6]
Bufotenium or as cinobufotenine is the quaternary ammonium cation form of bufotenidine, exhibits nicotine-like activity; activates nicotine-sensitive acetylcholine receptors.[7][8]
Differences
Cinobufotenine is similar to bufotenidine in that it does not readily cross the blood-brain barrier and is therefore peripherally selective. Cinobufotenine has very little activity or low affinity at the 5-hydroxytryptamine receptor, possessing less than one thousandth the potency of 5-hydroxytryptamine.[9][10] and also has a stimulation of cardiac activity, ten times less than the activity of adrenaline chloride, has a low miotic effect and increases the tone of the isolated intestine and uterus.[2]
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| Names | |
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| Preferred IUPAC name
3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-5-olate | |
| Other names
Bufotenidin; Cinobufagine; N,N,N-Trimethylserotonin; 5-Hydroxy-N,N,N-trimethyltryptammonium; 5-HTQ | |
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3D model (JSmol) |
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| ChemSpider | |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C13H18N2O | |
| Molar mass | 218.300 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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